Azo dye.



YLEOPDLDW EIESSE'AND OSCAR GUN rI-IER, or ELBERFELD, AND ARTHUR ZART, or VOHWIN- PATENT OFFICE.

UNITE- sratgls "KEL, NEAR ELBERFELD, GERMANY, ASSIGNORS TO FARBENFABRIKEN YORM. FRIEDR. V BAYER & C O.','OF' E LB ERFELD, GERMANY, A CQRPORATION O1 GERMANY.

AZO DYE. i

Specification of Letters Patent.

no: as 1 ,423. Patented. Aug. 17,-1909.

-App1ication filed. April 8,1909. Serial in. 488,698.

T 0 all w hom 'i t my concern:

the above given formula; and dyeing cotton y :2-benzoyl'amino-5-naphtho1-7-sulfonic. acid. Be it known that we, LEOPOLD Hnssn, OS- The combination is completed by the addi- CAR GI'JNTHER, and ARTHUR ZART, doctors of tion of sodium carbonate. The dye isophilosophy, chemists, citizens of the German lated in the usual way and purified by re-so- Empire, residing at, respectively, Elberfeld, lution in water. Itis, after being dried and Elberfeld, and Vohwinkel, near Elberfeld, pulverized, in the shape of] its sodiumsalt a Kingdom. of Prussia, Germany, have i-nreddish-brown powder which is soluble in vented new and useful Improvements in water with a red color a d which is soluble Azo Dyes, of which thefollowing is a speciin concentrated sulfuric acid with a blue fication. color. By reduction with stannous chlorid This-invention relates to the manufacture and hydrochloric acid para-sulfa'nilic acid, and productionv of new secondary diazo parra-phenylenediamin, and 2 benzoylaminodyestuffs dyeing cotton from red to blue (3-amino-5-naphtliol-7-sulfonic acid are obshades remarkable for their fastness to light. tained. The new dyestufi dyes cotton scar- They are obtained by combining diazotized let shades. aminoazo compounds with acidyli zed deriva- The process is carried out in an analogous tives of 2-amino5-naphthol compounds manner on using other initial compounds having'the formula: for the production of the aminoazo. comx pounds'e. g. anilin, meta-'aminobenzoic acid, ;S63H\/\/|VNHR ortho-aminobenzene sulfcnic acid, metal I aminobenzene su1fon1eacid, meta -xyl1din- J meta-sulfon c acid, para-chloroanihn-orthosulfonlc 8.03111, "para-nitranilinrmeta sulfonic acid, ortho-nitranililnpara-sulfonic acid, or

R meaning an acid radical, X meaning hyon using other aminsas second components rogen or SO H). for the production of the aminoazo com- 30 By the term aminoazo compounds we wish pounds, e. g. para xylidin, meta toluidin,

to point out that such aminoazo compounds cresidin, alpha-naphthylamin, alpha-naphare to be used as contain as first component thylamin-G- or 7 -sulfonic acid and other end a benzene derivative while the aminused com onents e. g. 2-ethylurethane-5-naphthol as second component may be either one of 7-su fonic' acid or L'Z-disulfonic acid, '5.5

the benzene or na hthalene. series. dioxy 7.7 disulfonie acid 2.2 dinaphthyl- The new dyestuiisare in the shape of their urea, acetyl 2.5- aminonaphthol-7 -su 1fonic alkaline salts dark powders easily soluble in acid, Q-methylur'ethane 5 naphthol 7 sulwater, solublein concentrated sulfuric acid fonic acid, Q-phenylurethane-5-naphthol-7- with from a violet to green' 'color U on 'Sulfonic acid, 2-phenylurea-5-naphthol-7-sul- .90 reduction with stannous' ehloridand 11y ro fonic acid, meta aminobeuzoy1-2.5 aminochloric acid the dyestuffs are decomposed, naphth01-7-su1fonic acid, etc. an amin of the benzene series, a diamin and We claim: an acidylized derivative of a 2.6-diamino-5- 1. The herein described new azo dyestuffs naphthol colnpoundhaving the formula: obtainable by combining the diazo comx p pounds of theliereinbefore defined aminoazo smHVVk/NHR compounds with acidylizcd derivatives of 2- I amino-fi-naphthol compounds of the above NH V given formula, which dyestuffs are, after 0 being dried and pulverized, in the shape of their alkaline salts dark powders soluble in are formed. water, so1uble in concentrated sulfuric acid In order to carry out this process we can with from a violet to green color; yieldin e. g. proceed as follows, the-parts being by upon reduction with stannous chlorid an weight zg299 parts of the sodium salt of hydrochloric acid an amin, of the benzene amino-azobenzene sulfonic acid are diazoseries, a. diamin and an acidylized derivative tized and the diazo compound is added to a of a 2.6-diamino-5-naphthol compound of solution of 365 parts of the sodium salt'of w from red to blue shade-s, substantially as 'de-zfi scribed.

2. The herein described new azo dyestuif diazoeminobenzene sulfonic acid, oara-phenyb enediamin and 2-benzoj'lamino-6-amino-5- naphthol-7-sulfonic acid; and dyeing cotwhich can be obtained by combinin tized aminoazobenzene sulfonic' acid with 2-henzo lamino-5-naphthol-7-su1fonic acid, set our hands in the presence of two su'bwhich yestufi' is, after being dried and ulscribing-witnesses. verized, in the shape of its. sodium sail: I LEOP OLD HESSE. [11.5.] reddish-brown powder which is soluble in ()SQAR GUNTHER a] Water with a. red color and which is soluble ARTHUR, Z AR'L in concentrated sulfuric acid with a blue Wit color; yielding upon reduction with stan- 0 Kij m nous chlorid and hydrochloric acid para- 0; J WRIGHT ton scarlet shades, sobstantiallg as described. In testimony whereof we ave hereunto It is hereby certified that in Letters Patent No. 931,?23, granted August 17, 1909,

huponthe anplication ot' Leopold Hesse and Oscar Gi'inther; of Elberfeld, and Arthur Zart, of Vohwinkeh nez r Elberfeld, Gerniany, for an imfirovement in Azo Dyes f I an error appears in printed specification requiring correction as follows: I n line 12 page 1,- the word diazo shonld read disazo; end thatthe said Letters Patent should be read with this correetionltherein that the sanie may conform to therecord of the case the Patent Ollice. I. i

Signed and sealed this 5th day of October, A. D., 1909. v

V ISEALI] I I I i 0. o. BILLINGS,

Acting Commissioner (4f w from red to blue shade-s, substantially as 'de-zfi scribed.

2. The herein described new azo dyestuif diazoeminobenzene sulfonic acid, oara-phenyb enediamin and 2-benzoj'lamino-6-amino-5- naphthol-7-sulfonic acid; and dyeing cotwhich can be obtained by combinin tized aminoazobenzene sulfonic' acid with 2-henzo lamino-5-naphthol-7-su1fonic acid, set our hands in the presence of two su'bwhich yestufi' is, after being dried and ulscribing-witnesses. verized, in the shape of its. sodium sail: I LEOP OLD HESSE. [11.5.] reddish-brown powder which is soluble in ()SQAR GUNTHER a] Water with a. red color and which is soluble ARTHUR, Z AR'L in concentrated sulfuric acid with a blue Wit color; yielding upon reduction with stan- 0 Kij m nous chlorid and hydrochloric acid para- 0; J WRIGHT ton scarlet shades, sobstantiallg as described. In testimony whereof we ave hereunto It is hereby certified that in Letters Patent No. 931,?23, granted August 17, 1909,

huponthe anplication ot' Leopold Hesse and Oscar Gi'inther; of Elberfeld, and Arthur Zart, of Vohwinkeh nez r Elberfeld, Gerniany, for an imfirovement in Azo Dyes f I an error appears in printed specification requiring correction as follows: I n line 12 page 1,- the word diazo shonld read disazo; end thatthe said Letters Patent should be read with this correetionltherein that the sanie may conform to therecord of the case the Patent Ollice. I. i

Signed and sealed this 5th day of October, A. D., 1909. v

V ISEALI] I I I i 0. o. BILLINGS,

Acting Commissioner (4f Lmters Patent No. 91,423.

Correction m It is hereby rertilied that in Letters Patent No. 931,423, granted August 17., 1909, upon the application of Leopold Hesse and OsearGfinther, 0f Elberfeld, and Arthur Zara, of Vohwinkel, near lfilherfeld, Germany, for an improvement in Azo Dyes," an error appears in the printed speoifir ation requiring correction as follows: In line 1; page I, the word diazo should read dz'sazo; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Oflice.

Signed and sealed this 5th day of October, A. D., 1909.

lSEAL. 1

o. o. BILLINGS, Acting (,hmmisfi oner qf .filtenta. 

